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CHEBI:66334 - xanthohumol B

ChEBI IDCHEBI:66334
ChEBI Namexanthohumol B
Stars
DefinitionA member of the class of chalcones that is (2E)-1-(3,4-dihydro-2H-chromen-6-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one substituted by hydroxy groups at position 3 and 5, a methoxy group at position 7 and geminal methyl groups at position 2. It has been isolated as a racemate from Humulus lupulus and has been shown to exhibit inhibitory activity against nitric oxide production.
Last Modified15 July 2013
DownloadsMolfile
FormulaC21H22O6
Net Charge0
Average Mass370.401
Monoisotopic Mass370.14164
SMILESCOc1cc2c(c(O)c1C(=O)/C=C/c1ccc(O)cc1)CC(O)C(C)(C)O2
InChIInChI=1S/C21H22O6/c1-21(2)18(24)10-14-16(27-21)11-17(26-3)19(20(14)25)15(23)9-6-12-4-7-13(22)8-5-12/h4-9,11,18,22,24-25H,10H2,1-3H3/b9-6+
InChIKeyGUQGMEWOCKDLDE-RMKNXTFCSA-N
Species of MetaboliteComponentSourceComments
Humulus lupulus (ncbitaxon:3486) - PubMed (15679315)
Roles Classification
Biological Roles:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
EC 1.14.13.39 (nitric oxide synthase) inhibitor  An EC 1.14.13.* (oxidoreductase acting on paired donors, incorporating 1 atom of oxygen, with NADH or NADPH as one donor) inhibitor that interferes with the action of nitric oxide synthase (EC 1.14.13.39).
ChEBI Ontology
Outgoing Relation(s)
xanthohumol B (CHEBI:66334) has role EC 1.14.13.39 (nitric oxide synthase) inhibitor (CHEBI:61908)
xanthohumol B (CHEBI:66334) has role metabolite (CHEBI:25212)
xanthohumol B (CHEBI:66334) is a aromatic ether (CHEBI:35618)
xanthohumol B (CHEBI:66334) is a chalcones (CHEBI:23086)
xanthohumol B (CHEBI:66334) is a polyphenol (CHEBI:26195)
IUPAC Name 
(2E)-1-(3,5-dihydroxy-7-methoxy-2,2-dimethyl-3,4-dihydro-2H-chromen-6-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one
Synonyms  Source
rac-6'',6''-dimethyl-5''-hydroxy-4'',5''-dihydropyrano[2'',3'':4',3']-4,2'-dihydroxy-6'-methoxychalconeChEBI
rac-(E)-1-(3,5-dihydroxy-7-methoxy-2,2-dimethyl-3,4-dihydrochromen-6-yl)-3-(4-hydroxyphenyl)prop-2-en-1-oneChEBI
rac-6-[3,4-dihydro-3,5-dihydroxy-7-methoxy-2,2-dimethyl-2H-benzo[b]pyrano]-3-(4-hydroxyphenyl)-2-propen-1-oneChEBI
Dehydrocycloxanthohumol hydrateLIPID MAPS
Manual XrefsDatabases
CPD-7127MetaCyc
LMPK12120299LIPID MAPS
HMDB0034867HMDB
EP2277526Patent
US2007218155Patent
WO2008095189Patent
Registry NumbersSources
Reaxys:7828262Reaxys
Citations